Hi Fleury,
Sounds like it made you nervous enough. What does your gut instinct tell you? It sounds very peculiar to me, too, and I'd report it. But then I live in an area where drug drops happen everywhere and the trafficking of drugs is very high. It could be nothing but then it could really be something bad going down each time. A call to your local police station won't cause any harm. That's a part of their job to check out suspicious situations.
For your own safety and peace of mind, maybe find another route to walk. Happy trails to you!
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